Exclusive Post-Retirement Interview with David Letterman

When we put together a local history of David Letterman for our May cover, the retiring television host promised us an interview shortly after he threw his final notecard. True to his word, he recently spent a few minutes chatting with Ron Pearson—a college buddy of his and a friend of the magazine—about what comes next.

How’s retirement treating you, Dave?

Very well. How was your weekend?

Wonderful. I took my grandson to his Little League baseball game.

So this is actual Little League, not coach-pitch?

No, this is the last year of coach-pitch. Next year, it’s the big leagues.

Yeah, that’s where my son, Harry, lost interest in baseball. I had forgotten that little kids who want to pitch do so as hard and fast as they can, and they don’t know what the hell they’re doing. Harry got clipped, and he said, “Jeez. I wasn’t counting on getting hurt.” Where does your grandson play ball?

Close to Dean Road and 79th Street. It’s not unusual to see a couple thousand people there on a Saturday.

That’s not far from where my mother and sister live. When I was in the Carmel area a couple of weeks ago, I was stunned by how that area has spread. It’s hard to imagine where all those people came from.

Actually, my wife, Sally, sees your mom on occasion.

Well, that’s probably more often than I do. She had a stroke a couple of weeks ago, but she’s fine. She’s 94, for heaven’s sake. If I had a stroke, I’d be hospitalized for the rest of my life. My mom has one, and she’s fine.

So the show is over. After decades of having professionals around to do your hair and makeup, who’s going to do those things for you now?

That’s certainly one of my primary concerns. I wasn’t born helpless, but when I first started doing the show, my manager said, “You’re going to need an assistant.” I asked why, and he said, “Well, you’ll need somebody to make phone calls.” And I thought, I can’t make my own calls? As it turns out, after all these years of having someone make my calls for me, I can no longer operate a telephone. I don’t know what to do with my hair, either. But I’ll never wear makeup again, so that’s no problem.

I’ve been blessed to have a few great executive assistants over the years, and I’ve had some pleasant conversations with yours, Mary Barclay. Will she stay on with you now that you’re retired?

Yes, I’m happy that two of the women who have worked with me will continue doing so for awhile. It’s stunning what you find out about yourself when everything you’ve done for 33 years changes. It’s like ice melting out from under you. I know that regular, responsible people probably hear me whining like this and think, Oh, brother. But I’m trying to rehabilitate myself, so keep me in your thoughts and prayers.

Speaking of prayers, did you ever say one before interviewing someone you were particularly anxious about hosting?

I wouldn’t call it a prayer, but I would sometimes have a conversation with myself in the shower before the show. Warren Zevon was on years ago, and we all knew he was dying. I was at a loss because I couldn’t think of an entry point for a conversation with a dying man on a television show that’s supposed to be silly. “How are you doing? You look great!” doesn’t exactly work. I was really dissatisfied with my part of that conversation. I was ill-equipped to connect with a friend who was going through something like that. And the first time Bill Clinton was on the show, I was a little anxious for totally different reasons. Of course, what I learned about Bill was that you don’t even need to be in the studio for that interview. He’ll take care of it.

I saw images of you at the Indianapolis 500 this year. I remember in college you said that you thought the 500 should go from Indy to Kansas City so more people could see the race.

[laughs] Everybody would have a straightaway seat!

Are you planning on attending more IndyCar races now that you’re retired?

I should just say “Yes.” But as with a lot of sports, it really is better at home watching it on TV. Because the 500 takes place in my hometown, I almost always go. Were you aware, though, that race fans sometimes have something to drink at the race? They want to come up and lick me. I’m not saying anything negative about Indianapolis or the race fans there, because I am one of them.

What are your other hobbies these days?

I love fishing with my son. Any kind of trout fishing where you can stand in the river is just delightful. I don’t know what I’m doing, but I can stand in the river. I’m pretty good at that. And isn’t that 90 percent of it?

Do you ever sneak into Victory Field for an Indians game?

Yes, my wife and I went a few years ago. They played the Louisville River Dogs or something like that. Every time I drive by the old Bush Stadium, it makes me sad, because that was my first experience with baseball. Now it’s condos. If you’re going to take down part of that beautiful brick wall, just blow the place up. It was such a cool old park.

What other changes have you noticed in Indianapolis?

Well, Mass Ave looks totally different. It’s like China, where they put up a skyscraper in an afternoon.

Do you keep up with the local news?

Yes, I see that they’re going to start handing out tickets for going slow in the fast lane. It’s going to be a demolition derby on I-465.

How about Ball State sports? Are you watching those on some obscure cable channel late at night?

I think they do really well in volleyball. If I were a betting man, I’d bet on Ball State women’s volleyball. Of course, you’d need to find one of those offshore bookies.

Cycling seems like a good retirement hobby for you. As I recall, you liked to ride. Do you throw your leg over a bike anymore?

I do on occasion. But as I get older, I’m starting to realize that I don’t want to be found dead in a ditch somewhere. I’ll leave cycling to younger men.